DE1927918C3 - Sulfogruppenhaltige Disazofarbstoffe, Verfahren zu ihrer Herstellung und deren Verwendung zum Färben synthetischer Fasermaterialien - Google Patents
Sulfogruppenhaltige Disazofarbstoffe, Verfahren zu ihrer Herstellung und deren Verwendung zum Färben synthetischer FasermaterialienInfo
- Publication number
- DE1927918C3 DE1927918C3 DE19691927918 DE1927918A DE1927918C3 DE 1927918 C3 DE1927918 C3 DE 1927918C3 DE 19691927918 DE19691927918 DE 19691927918 DE 1927918 A DE1927918 A DE 1927918A DE 1927918 C3 DE1927918 C3 DE 1927918C3
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- dyes
- dye
- synthetic fiber
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000975 dye Substances 0.000 title claims description 38
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 4
- 238000004043 dyeing Methods 0.000 title description 7
- 239000000463 material Substances 0.000 title description 6
- 239000012209 synthetic fiber Substances 0.000 title description 5
- 229920002994 synthetic fiber Polymers 0.000 title description 5
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 title description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000004952 Polyamide Substances 0.000 description 16
- 229920002647 polyamide Polymers 0.000 description 16
- 239000000243 solution Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000008878 coupling Effects 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- 238000005859 coupling reaction Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 5
- 239000002168 alkylating agent Substances 0.000 description 4
- 229940100198 alkylating agent Drugs 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- -1 Alkoxy-amino compound Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 150000002828 nitro derivatives Chemical class 0.000 description 3
- ZCLXQTGLKVQKFD-UHFFFAOYSA-N 3-hydroxybenzenesulfonic acid Chemical compound OC1=CC=CC(S(O)(=O)=O)=C1 ZCLXQTGLKVQKFD-UHFFFAOYSA-N 0.000 description 2
- JXZGTFLJFKLVAX-UHFFFAOYSA-N 5-amino-2-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(N)C=C1S(O)(=O)=O JXZGTFLJFKLVAX-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 2
- 229940008406 diethyl sulfate Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000003855 acyl compounds Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- BJOUHCXNFKNXBL-UHFFFAOYSA-N anilinosulfamic acid Chemical compound OS(=O)(=O)NNC1=CC=CC=C1 BJOUHCXNFKNXBL-UHFFFAOYSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- CHMBIJAOCISYEW-UHFFFAOYSA-N n-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/06—Disazo dyes from a coupling component "C" containing a directive hydroxyl group
- C09B31/062—Phenols
- C09B31/065—Phenols containing acid groups, e.g. —CO2H, —SO3H, —PO3H2, —OSO3H, —OPO2H2; Salts thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/28—Preparation of azo dyes from other azo compounds by etherification of hydroxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691927918 DE1927918C3 (de) | 1969-05-31 | 1969-05-31 | Sulfogruppenhaltige Disazofarbstoffe, Verfahren zu ihrer Herstellung und deren Verwendung zum Färben synthetischer Fasermaterialien |
| CH78072A CH565840A5 (enrdf_load_stackoverflow) | 1969-05-31 | 1970-05-08 | |
| CA082393A CA927378A (en) | 1969-05-31 | 1970-05-11 | Disazo dyestuffs |
| GB2288170A GB1281989A (en) | 1969-05-31 | 1970-05-12 | Disazo dyestuffs |
| NL7007229A NL7007229A (enrdf_load_stackoverflow) | 1969-05-31 | 1970-05-19 | |
| BE751172D BE751172A (fr) | 1969-05-31 | 1970-05-29 | Nouveaux colorants disazoiques |
| FR7019901A FR2043870B1 (enrdf_load_stackoverflow) | 1969-05-31 | 1970-05-29 | |
| US05/328,436 US3997522A (en) | 1969-05-31 | 1973-01-31 | Disazo dyestuffs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691927918 DE1927918C3 (de) | 1969-05-31 | 1969-05-31 | Sulfogruppenhaltige Disazofarbstoffe, Verfahren zu ihrer Herstellung und deren Verwendung zum Färben synthetischer Fasermaterialien |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1927918A1 DE1927918A1 (de) | 1970-12-03 |
| DE1927918B2 DE1927918B2 (de) | 1977-08-25 |
| DE1927918C3 true DE1927918C3 (de) | 1978-06-08 |
Family
ID=5735808
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691927918 Expired DE1927918C3 (de) | 1969-05-31 | 1969-05-31 | Sulfogruppenhaltige Disazofarbstoffe, Verfahren zu ihrer Herstellung und deren Verwendung zum Färben synthetischer Fasermaterialien |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE751172A (enrdf_load_stackoverflow) |
| CA (1) | CA927378A (enrdf_load_stackoverflow) |
| CH (1) | CH565840A5 (enrdf_load_stackoverflow) |
| DE (1) | DE1927918C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2043870B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1281989A (enrdf_load_stackoverflow) |
| NL (1) | NL7007229A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3237369A1 (de) * | 1982-10-08 | 1984-04-12 | Bayer Ag, 5090 Leverkusen | Disazofarbstoffe |
| JP2000186222A (ja) | 1998-12-22 | 2000-07-04 | Mitsubishi Chemicals Corp | 感熱転写用ジスアゾ系色素、及びそれを用いた感熱転写用シート並びに感熱転写用インク |
-
1969
- 1969-05-31 DE DE19691927918 patent/DE1927918C3/de not_active Expired
-
1970
- 1970-05-08 CH CH78072A patent/CH565840A5/xx not_active IP Right Cessation
- 1970-05-11 CA CA082393A patent/CA927378A/en not_active Expired
- 1970-05-12 GB GB2288170A patent/GB1281989A/en not_active Expired
- 1970-05-19 NL NL7007229A patent/NL7007229A/xx unknown
- 1970-05-29 BE BE751172D patent/BE751172A/xx unknown
- 1970-05-29 FR FR7019901A patent/FR2043870B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE751172A (fr) | 1970-11-03 |
| DE1927918A1 (de) | 1970-12-03 |
| NL7007229A (enrdf_load_stackoverflow) | 1970-12-02 |
| GB1281989A (en) | 1972-07-19 |
| FR2043870B1 (enrdf_load_stackoverflow) | 1974-08-09 |
| DE1927918B2 (de) | 1977-08-25 |
| CA927378A (en) | 1973-05-29 |
| FR2043870A1 (enrdf_load_stackoverflow) | 1971-02-19 |
| CH565840A5 (enrdf_load_stackoverflow) | 1975-08-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |